Acetic Acid → 2-Cyano-3-phenylprop-2-enoic acid

HRID 358122Notes

Reaction equation

HRID 358122 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][C:12]([OH:14])=[O:13])#[N:10].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C(O)C>[C:9]([C:11](=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([OH:14])=[O:13])#[N:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 9740Cyanoacetic acidHCID 517165Ammonium Acetate

Product 1

HCID 705342-Cyano-3-phenylprop-2-enoic acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 g of benzaldehyde, 176 g of cyanoacetic acid, 30 ml of acetic acid and 14.5 g of ammonium acetate were refluxed for 4 hours in 800 ml of ethyl alcohol with heating. After the reaction, the mixture was concentrated to 400 ml by removing the ethyl alcohol under a reduced pressure, followed by pouring into 1 liter of ice water to separate crystals. The resulting crystals were recrystallized from 250 ml of acetonitrile to obtain 265 g of 2-cyano-3-phenylacrylic acid having a melting point of 184° to 188° C. 150 g of the resulting compound and 176 g of thionyl chloride were dissolved in 100 ml of acetonitrile with heating for 1 hour. After the reaction, the acetonitrile and the thionyl chloride were distilled off under a reduced pressure, and the resulting solid was added to a solution containing 124 g of hydroxyethyl methacrylate, 75 g of pyridine and 1 liter of acetonitrile. The reaction was carried out for 2 hours while maintaining the reaction temperature below 40° C. After the reaction, the reacting solution was poured into ice water to separate crystals, and the resulting crystals were recrystallized from 1 liter of ethyl alcohol to obtain 205 g of the desired compound having a melting point of 68° to 70° C. The identification of the compound was carried out using IR spectrum, NMR spectrum and elemental analysis.

Workup

  1. temperaturewith heating
  2. customAfter the reaction
  3. concentrationthe mixture was concentrated to 400 ml
  4. customby removing the ethyl alcohol under a reduced pressure
  5. additionby pouring into 1 liter of ice water
  6. customto separate crystals
  7. customThe resulting crystals were recrystallized from 250 ml of acetonitrile

Sources & evidence

ORD record
ord-22c23c816ff3404281a7454c1401fa9a
Source dataset
uspto-grants-1984_08
Patent number
US04464463

Reaction notes

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